Synthesis of cyclic 2-enones from cyclic 1,3-diketones
About: This article is published in Journal of Organic Chemistry.The article was published on 1973-10-01. It has received 29 citations till now.
Citations
More filters
TL;DR: Syntheses of condensed tri-, tetra-and pentacyclic thiazolo[3,2-a]pyrimidine systems are described in this paper. But they do not discuss the relation between condensed tri, tetra, and tetra systems.
Abstract: Syntheses of condensed tri-, tetra- and pentacyclic thiazolo[3,2-a]pyrimidine systems are described.
2 citations
01 Jan 2000
1 citations
TL;DR: A formal synthesis of (±)-isodihydronepetalactone from cyclobutenone 5 was de scribed in this article, where the synthesis was carried out using the Shapiro reaction on hydrazone derivative in the presence of excess dry ice.
Abstract: A formal synthesis of (±)-isodihydronepetalactone (1) from cyclobutenone 5 was de scribed. Baeyer-Villiger lactonization of cyclobutanone 8 followed by decholorination led to lactone 4, which under went a series of functional group trans formations, furnished cyclopentanone derivative 15. Shapiro reaction on hydrazone derivative in the presence of excess dry ice gave lactone 2. Lactone 2 had previously been converted to isodihydronepetalactone (1).
1 citations
TL;DR: In this paper , an unexpected 1,5 nitrogen to carbon tosyl migration was reported, resulting in the isolation of an unusual sulfonated dimedone. But the mechanism of this migration is unknown.
Abstract: Controlled sulfonyl migration is considered an important transformation for total synthesis, and scaffold elaboration. Accordingly, efforts to understand the underlying properties of these often serendipitously identified reactions have important implications. Following the attempted synthesis of a tetrahydroindazolone analogue, we report here an unexpected 1,5 nitrogen to carbon tosyl migration, resulting in the isolation of an unusual sulfonated dimedone. Synthetic and mechanistic investigations provide early insight into the scope of this reaction, with two potential mechanisms proposed.